SK38599A3 - Derivates of piperidine-ketocarboxylic acid, their preparation and use - Google Patents
Derivates of piperidine-ketocarboxylic acid, their preparation and use Download PDFInfo
- Publication number
- SK38599A3 SK38599A3 SK385-99A SK38599A SK38599A3 SK 38599 A3 SK38599 A3 SK 38599A3 SK 38599 A SK38599 A SK 38599A SK 38599 A3 SK38599 A3 SK 38599A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- piperidine
- phenyl
- general formula
- treatment
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000002253 acid Substances 0.000 title claims description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
- 239000003112 inhibitor Substances 0.000 claims description 25
- 108010032088 Calpain Proteins 0.000 claims description 24
- 102000007590 Calpain Human genes 0.000 claims description 24
- -1 CF 3 Inorganic materials 0.000 claims description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 102000005927 Cysteine Proteases Human genes 0.000 claims description 11
- 108010005843 Cysteine Proteases Proteins 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Chemical group 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
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- 230000004054 inflammatory process Effects 0.000 claims description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
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- 238000002399 angioplasty Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 208000001286 intracranial vasospasm Diseases 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
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- 210000002027 skeletal muscle Anatomy 0.000 claims description 2
- 210000000329 smooth muscle myocyte Anatomy 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 5
- 230000003961 neuronal insult Effects 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229940126534 drug product Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 108010079785 calpain inhibitors Proteins 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 12
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 239000011575 calcium Substances 0.000 description 10
- 229910052791 calcium Inorganic materials 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 8
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- 239000012074 organic phase Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 150000007513 acids Chemical class 0.000 description 6
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- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Neurology (AREA)
- Biomedical Technology (AREA)
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- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19642591A DE19642591A1 (de) | 1996-10-15 | 1996-10-15 | Neue Piperidin-Ketocarbonsäure-Derivate, deren Herstellung und Anwendung |
| PCT/EP1997/005202 WO1998016512A1 (de) | 1996-10-15 | 1997-09-23 | Neue piperidin-ketocarbonsäure-derivate, deren herstellung und anwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK38599A3 true SK38599A3 (en) | 2000-04-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK385-99A SK38599A3 (en) | 1996-10-15 | 1997-09-23 | Derivates of piperidine-ketocarboxylic acid, their preparation and use |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6380220B1 (cs) |
| EP (1) | EP0934273A1 (cs) |
| JP (1) | JP2001501955A (cs) |
| KR (1) | KR20000049130A (cs) |
| CN (1) | CN1239950A (cs) |
| AR (1) | AR009379A1 (cs) |
| AU (1) | AU736754B2 (cs) |
| BG (1) | BG103338A (cs) |
| BR (1) | BR9711908A (cs) |
| CA (1) | CA2268917A1 (cs) |
| CO (1) | CO4930264A1 (cs) |
| CZ (1) | CZ126899A3 (cs) |
| DE (1) | DE19642591A1 (cs) |
| HR (1) | HRP970549A2 (cs) |
| HU (1) | HUP9904104A3 (cs) |
| IL (1) | IL129089A0 (cs) |
| NO (1) | NO991761L (cs) |
| NZ (1) | NZ334979A (cs) |
| PL (1) | PL332720A1 (cs) |
| RU (1) | RU2189974C2 (cs) |
| SK (1) | SK38599A3 (cs) |
| TR (1) | TR199900819T2 (cs) |
| WO (1) | WO1998016512A1 (cs) |
| ZA (1) | ZA979175B (cs) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9909773A (pt) | 1998-04-20 | 2000-12-19 | Basf Ag | Amida heterociclicamente substituìda, uso da mesma, e, preparação farmacêutica para uso oral, parenteral e intraperitoneal |
| CA2328396C (en) | 1998-04-20 | 2009-02-10 | Basf Aktiengesellschaft | New substituted amides, their production and their use |
| DE19817459A1 (de) * | 1998-04-20 | 1999-10-21 | Basf Ag | Neue heterozyklische substituierte Amide, Herstellung und Anwendung |
| KR20010042839A (ko) * | 1998-04-20 | 2001-05-25 | 스타르크, 카르크 | 시스테인 프로테아제를 억제하는 효과를 나타내고헤테로시클릭 치환체가 있는 신규 아미드 |
| US6117870A (en) * | 1998-11-12 | 2000-09-12 | Fujirebio Kabushiki Kaisha | Cyclic amide derivatives |
| AU6936500A (en) * | 1999-08-24 | 2001-03-19 | Regents Of The University Of California, The | Non-quinoline inhibitors of malaria parasites |
| DE60021521T4 (de) | 1999-09-29 | 2006-09-21 | Ortho-Mcneil Pharmaceutical, Inc. | Isonipecotamide zur behandlung von integrin vermittelten störungen |
| EP2289888A3 (en) | 2000-06-30 | 2011-07-13 | Seikagaku Corporation | Epoxycarboxylic acid amides, azides and amino alcohols and processes for preparation of alpha-keto amides by using them |
| DE10114762A1 (de) * | 2001-03-26 | 2002-10-02 | Knoll Gmbh | Verwendung von Cysteinprotease-Inhibitoren |
| US7081460B2 (en) | 2001-04-09 | 2006-07-25 | Ortho-Mcneil Pharmaceutical, Inc. | Quinazoline and quinazoline-like compounds for the treatment of integrin-mediated disorders |
| AU2003267991B2 (en) | 2002-07-11 | 2009-10-08 | Vicuron Pharmaceuticals, Inc. | N-hydroxyamide derivatives possessing antibacterial activity |
| WO2005016883A2 (en) * | 2003-08-14 | 2005-02-24 | Icos Corporation | Acrylamide derivatives as vla-1 integrin antagonists and uses thereof |
| KR20070008517A (ko) * | 2003-10-24 | 2007-01-17 | 아벤티스 파마슈티칼스 인크. | 카텝신 저해물질로서 신규한 케토-옥사디아졸 유도체 |
| PT2439205E (pt) | 2006-12-29 | 2015-07-16 | Abbvie Deutschland | Compostos de carboxamida e seus usos como inibidores de calpaína |
| TWI453019B (zh) * | 2007-12-28 | 2014-09-21 | Abbvie Deutschland | 甲醯胺化合物 |
| TWI519530B (zh) * | 2009-02-20 | 2016-02-01 | 艾伯維德國有限及兩合公司 | 羰醯胺化合物及其作為鈣蛋白酶（ｃａｌｐａｉｎ）抑制劑之用途 |
| US8236798B2 (en) * | 2009-05-07 | 2012-08-07 | Abbott Gmbh & Co. Kg | Carboxamide compounds and their use as calpain inhibitors |
| US9051304B2 (en) | 2009-12-22 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Carboxamide compounds and their use as calpain inhibitors V |
| US8598211B2 (en) * | 2009-12-22 | 2013-12-03 | Abbvie Inc. | Carboxamide compounds and their use as calpain inhibitors IV |
| US9062027B2 (en) | 2010-12-09 | 2015-06-23 | AbbVie Deutschland GmbH & Co. KG | Carboxamide compounds and their use as calpain inhibitors V |
| SG11201406345XA (en) | 2012-04-03 | 2014-11-27 | Abbvie Deutschland | Carboxamide compounds and their use as calpain inhibitors v |
| EP3426674A4 (en) | 2016-03-09 | 2019-08-14 | Blade Therapeutics, Inc. | CYCLIC KETO AMID COMPOUNDS AS CALPAIN MODULATORS AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| EP3481835A4 (en) | 2016-07-05 | 2020-02-26 | Blade Therapeutics, Inc. | CALPAIN MODULATORS AND THERAPEUTIC USE THEREOF |
| SG10201912574WA (en) | 2016-09-28 | 2020-02-27 | Blade Therapeutics Inc | Calpain modulators and therapeutic uses thereof |
| CN110545812A (zh) | 2017-06-01 | 2019-12-06 | 卫材R&D管理有限公司 | 包含pde9抑制剂的药物组合物 |
| CA3061884A1 (en) | 2017-06-01 | 2019-10-29 | Eisai R&D Management Co., Ltd. | Lewy body disease therapeutic agent containing pyrazoloquinoline derivative |
| SG11202008750XA (en) * | 2018-03-28 | 2020-10-29 | Blade Therapeutics Inc | Calpain modulators and therapeutic uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8904298D0 (sv) * | 1989-12-21 | 1989-12-21 | Astra Ab | New compounds |
| WO1992011850A2 (en) * | 1990-12-28 | 1992-07-23 | Cortex Pharmaceuticals, Inc. | Use of calpain inhibitors in the inhibition and treatment of neurodegeneration |
| CA2098702A1 (en) * | 1990-12-28 | 1992-06-29 | James C. Powers | Peptide ketoamides, ketoacids, and ketoesters |
| CA2071621C (en) * | 1991-06-19 | 1996-08-06 | Ahihiko Hosoda | Aldehyde derivatives |
| EP0650368A1 (en) * | 1992-06-24 | 1995-05-03 | Cortex Pharmaceuticals, Inc. | Use of calpain inhibitors in the inhibition and treatment of medical conditions associated with increased calpain activity |
| US5541290A (en) * | 1993-06-24 | 1996-07-30 | Harbeson; Scott L. | Optically pure calpain inhibitor compounds |
-
1996
- 1996-10-15 DE DE19642591A patent/DE19642591A1/de not_active Withdrawn
-
1997
- 1997-09-23 CN CN97180507A patent/CN1239950A/zh active Pending
- 1997-09-23 RU RU99109969/04A patent/RU2189974C2/ru active
- 1997-09-23 HU HU9904104A patent/HUP9904104A3/hu unknown
- 1997-09-23 IL IL12908997A patent/IL129089A0/xx unknown
- 1997-09-23 CZ CZ991268A patent/CZ126899A3/cs unknown
- 1997-09-23 KR KR1019990703216A patent/KR20000049130A/ko not_active Withdrawn
- 1997-09-23 EP EP97910332A patent/EP0934273A1/de not_active Withdrawn
- 1997-09-23 PL PL97332720A patent/PL332720A1/xx unknown
- 1997-09-23 BR BR9711908A patent/BR9711908A/pt unknown
- 1997-09-23 CA CA002268917A patent/CA2268917A1/en not_active Abandoned
- 1997-09-23 TR TR1999/00819T patent/TR199900819T2/xx unknown
- 1997-09-23 US US09/284,543 patent/US6380220B1/en not_active Expired - Fee Related
- 1997-09-23 WO PCT/EP1997/005202 patent/WO1998016512A1/de not_active Ceased
- 1997-09-23 JP JP10517955A patent/JP2001501955A/ja active Pending
- 1997-09-23 SK SK385-99A patent/SK38599A3/sk unknown
- 1997-09-23 NZ NZ334979A patent/NZ334979A/en unknown
- 1997-09-23 AU AU47770/97A patent/AU736754B2/en not_active Ceased
- 1997-10-14 ZA ZA979175A patent/ZA979175B/xx unknown
- 1997-10-14 CO CO97060053A patent/CO4930264A1/es unknown
- 1997-10-14 AR ARP970104718A patent/AR009379A1/es not_active Application Discontinuation
- 1997-10-14 HR HR19642591,3A patent/HRP970549A2/hr not_active Application Discontinuation
-
1999
- 1999-04-14 NO NO991761A patent/NO991761L/no not_active Application Discontinuation
- 1999-04-15 BG BG103338A patent/BG103338A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001501955A (ja) | 2001-02-13 |
| AU736754B2 (en) | 2001-08-02 |
| ZA979175B (en) | 1999-04-14 |
| HUP9904104A3 (en) | 2001-01-29 |
| CZ126899A3 (cs) | 1999-07-14 |
| RU2189974C2 (ru) | 2002-09-27 |
| AU4777097A (en) | 1998-05-11 |
| IL129089A0 (en) | 2000-02-17 |
| KR20000049130A (ko) | 2000-07-25 |
| HRP970549A2 (en) | 1998-08-31 |
| HUP9904104A2 (hu) | 2000-05-28 |
| WO1998016512A1 (de) | 1998-04-23 |
| PL332720A1 (en) | 1999-10-11 |
| BR9711908A (pt) | 1999-08-24 |
| DE19642591A1 (de) | 1998-04-16 |
| AR009379A1 (es) | 2000-04-12 |
| CN1239950A (zh) | 1999-12-29 |
| NZ334979A (en) | 2001-02-23 |
| CA2268917A1 (en) | 1998-04-23 |
| NO991761D0 (no) | 1999-04-14 |
| BG103338A (bg) | 2000-01-31 |
| TR199900819T2 (xx) | 1999-06-21 |
| US6380220B1 (en) | 2002-04-30 |
| NO991761L (no) | 1999-04-14 |
| CO4930264A1 (es) | 2000-06-27 |
| EP0934273A1 (de) | 1999-08-11 |
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